An expeditious construction of polycyclic ketals: synthesis of fused seven-membered rings and substituted naphthalenes

Authors
Hanna, I Michaut, V Ricard, L
Citation
I. Hanna et al., An expeditious construction of polycyclic ketals: synthesis of fused seven-membered rings and substituted naphthalenes, TETRAHEDR L, 42(2), 2001, pp. 231-234
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
2
Year of publication
2001
Pages
231 - 234
Database
ISI
SICI code
0040-4039(20010108)42:2<231:AECOPK>2.0.ZU;2-9
Abstract
Treatment of allylic alcohols 5, easily prepared from dioxene and methoxyac etophenones, with 1-(trimethylsilyloxy)cyclopentene in the presence of a ca talytic amount of TMSOTf in acetonitrile, afforded a polycyclic acetal 6 by domino nucleophilic substitution, annulation and intramolecular Friedel-Cr afts alkylation reaction sequence. Acid-mediated cleavage of the acetal moi ety led to fused seven-membered carbocyclic rings or to substituted naphtha lenes. (C) 2000 Elsevier Science Ltd. All rights reserved.